Lesson Two: Plan Multiple Steps Ahead
The Raptors have notoriously been criticized for their lack of foresight, spanning all the way back to the infamous Jakob Poeltl trade which has left Toronto at risk of conceding their 2024 lottery pick. However, the most egregious example of this bad habit was their response to the loss of Fred Vanvleet during the 2023 off-season.
It was obvious amongst league circles that VanVleet would likely decline any deal the Raptors made in favor of a more lucrative salary from an outside suitor. Nevertheless, the Raptors still somehow managed to be caught off-guard by his departure and responded by giving multi-year deals to Dennis Schroder and Jalen McDaniels. Flash-forward one season, Schroder has been sent off to Brooklyn for cap flexibility, and McDaniels has had one of the least efficient seasons imaginable, shooting 34 percent from the field and 16.9 percent from three.
This issue emerged once again before the trade deadline, where the Raptors sent their franchise forward Pascal Siakam to the Pacers in exchange for a puzzling package of Bruce Brown, Kira Lewis Jr., Jordan Nwora, and three first-round picks. The Raptors managed to back themselves into a corner with this one, as their unwillingness to commit to a direction the season before had tanked Siakam's value, who was expected to pursue free agency at the end of the year.
Though the 3 first-rounders (now 2 due to the Olynyk/Agbaji trade) somewhat salvaged this deal, it is clear that the value the Raptors received is nowhere deal what they parted with, and their hesitancy to prioritize the future ultimately ended up damaging what could have been an extremely lucrative return.